Methylamine → 4-Nitro-(2-methylaminoethoxy)benzene

HRID 322631

Reaction equation

HRID 322631 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][NH2:15]>C(O)(C)C.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:15][CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 27645871-(2-Chloroethoxy)-4-nitrobenzene

Product 1

HCID 122944674-Nitro-(2-methylaminoethoxy)benzene

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-nitro-(2-chloroethoxy)benzene (781 mg, 3.9 mmol) and aqueous methylamine (15 mL, 40 wt. %) in isopropyl alcohol (15 mL) is heated in a sealed tube at 100° for 4 hours. After cooling in an ice water bath, the mixtured is poured into brine and extracted 2× with dichloromethane, dried over sodium sulfate, filtered, and concentrated in vacuo to give 4-nitro-(2-methylaminoethoxy)benzene (697 mg).

Workup

  1. temperatureis heated in a sealed tube at 100° for 4 hours
  2. temperatureAfter cooling in an ice water bath
  3. extractionextracted 2× with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab2a837b24004feb9e81f2c4770ebd7d
Source dataset
uspto-grants-2001_04
Patent number
US06211365B1

Linked notes

Loading…